- Thallium trinitrate-mediated ring contraction of 1,2-dihydronaphthalenes: An approach to the synthesis of indans
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Oxidation of 1,2-dihydronaphthalenes with thallium trinitrate was studied. 1,2-dihydronaphthalene, 1-methyl-1,2-dihydronaphthalene, 6- and 8-methoxy-1,2-dihydronaphthalenes gave rise to the respective ring contraction products in good yields, whereas the
- Ferraz, Helena M.C,Silva Jr., Luiz F,Vieira, Tiago O
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- Metal-free synthesis of indanes by iodine(iii)-mediated ring contraction of 1,2-dihydronaphthalenes
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A metal-free protocol was developed to synthesize indanes by ring contraction of 1,2-dihydronaphthalenes promoted by PhI(OH)OTs (HTIB or Koser's reagent). This oxidative rearrangement can be performed in several solvents (MeOH, CH3CN, 2,2,2-trifluoroethanol (TFE), 1,1,1,3,3,3-hexafluoroisopropanol (HFIP), and a 1:4 mixture of TFE:CH2Cl2) under mild conditions. The ring contraction diastereoselectively gives functionalized trans-1,3-disubstituted indanes, which are difficult to obtain in synthetic organic chemistry. ?2011 Sociedade Brasileira de Qui?mica.
- Siqueira, Fernanda A.,Ishikawa, Eloisa E.,Fogac?a, Andre?,Faccio, Andre?a T.,Carneiro, Va?nia M. T.,Soares, Rafael R. S.,Utaka, Aline,Te?be?ka, Iris R. M.,Bielawski, Marcin,Olofsson, Berit,Silva Jr., Luiz F.
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experimental part
p. 1795 - 1807
(2012/06/01)
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- A new titanium tetrachloride mediated annulation of α -aryl-substituted carbonyl compounds with alkynes: A simple and highly efficient method for the regioselective synthesis of polysubstituted naphthalene derivatives
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A new straightforward procedure has been developed for the synthesis of polysubstituted naphthalene derivatives. The reaction of α -aryl-substituted carbonyl compounds with terminal or internal alkynes in the presence of TiCl4 regioselectively generates substituted naphthalene derivatives in good to excellent yields.
- Kabalka, George W.,Ju, Yuhong,Wu, Zhongzhi
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p. 7915 - 7917
(2007/10/03)
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- REDUCTIVE ACTIVATION OF ARENES IX. REACTION OF THE PRODUCTS FROM TWO-ELECTRON REDUCTION OF BENZONITRILE AND 1-NAPHTHONITRILE WITH ALKYL HALIDES IN LIQUID AMMONIA
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The action of alkyl bromides and iodides on the sodium and potassium salts of the 1-cyanocyclohexa-2,5-dien-1-yl and 1-cyano-1,4-dihydro-1-naphthyl anions, obtained during two-electron reduction of benzonitrile and 1-naphthonitrile in liquid ammonia, gives the corresponding alkylarenes and 1-cyano-1-alkyl-1,4-dihydroarenes.Butyl chloride acts as a protonating agent toward the above-mentioned anions.The effects of the nature of the aryl fragment, the alkyl halide, and the order of mixing of the reagents on the ratio of the main reaction products were determined.
- Bil'kis, I.I.,Vaganova, T.A.,Shteingarts, V.D.
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p. 951 - 956
(2007/10/02)
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- Competitive Dienone-Phenol Type Rearrangements for the Regioselective Preparation of 2,4-Disubstituted-Naphth-1-ols
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The regioselective preparation of 2,4-substituted-naphth-1-ols via a variant of the dienone-phenol rearrangement is described.
- Dodge, Jeffrey A.,Chamberlin, A. Richard
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p. 4827 - 4830
(2007/10/02)
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